(R)-2-(cyclohexanecarboxamido)propanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-(cyclohexanecarboxamido)propanoic acid
• 英文别名: (2R)-2-[(Cyclohexylcarbonyl)amino]propanoic acid；(2R)-2-(cyclohexanecarbonylamino)propanoic acid
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: LYBZCFYXVCCLLS-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(cyclohexanecarboxamido)propanoic acid 在 Grubbs catalyst first generation 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 E/Z-Monoene A
  参考文献：
  名称：

  Monoenomycin: A Simplified Trienomycin A Analogue That Manifests Anticancer Activity

  摘要：

  Macrocydic natural products are a powerful class of leadlike chemical entities. Despite commonly violating Lipinski's "rule of 5", these compounds often demonstrate superior druglike physicochemical and pharmacokinetic attributes when compared to their acyclic counterparts. However, the elaborate structural architectures of such molecules require rigorous synthetic investigation that complicates analogue development and their application to drug discovery programs. To circumvent these limitations, a conformation-based approach using limited structure-activity relationships and molecular modeling was implemented to design simplified analogues of trienomycin A, in which the corresponding analogues could be prepared in a succinct manner to rapidly identify essential structural components necessary for biological activity. Trienomycin A is a member of the ansamycin family of natural products that possesses potent anticancer activity. These studies revealed a novel trienomycin A analogue, rnonoenomycin, which manifests potent anticancer activity.

  DOI：

  10.1021/ml200108y
• 作为产物：
  描述：

  methyl (cyclohexanecarbonyl)alaninate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以95 %的产率得到(R)-2-(cyclohexanecarboxamido)propanoic acid
  参考文献：
  名称：

  三烯霉素 A 简化类似物：合成和抗神经炎症活性

  摘要：

  已设计、合成并评估了一系列新型三烯霉素 A ( TA ) 模拟化合物 ( 5a–p )的体外抗神经炎症和神经保护活性。其中，化合物5h、5n和5o对LPS 激活的BV-2 细胞表现出较强的NO 抑制活性，EC 50值分别为12.4、17.3 和8.9 μM。此外，5h在 20 μM 时对 H 2 O 2诱导的 PC-12 细胞显示出明显的神经保护作用而没有细胞毒性。总的来说，这些化合物可以提供对结构-活性关系的更好理解TA并提供抗神经炎症和神经保护剂的研究思路。

  DOI：

  10.1016/j.bmcl.2022.129122

文献信息

• (+)-Thiazinotrienomycin E: Relative and absolute stereochemistry
  作者：Amos B Smith、Joseph Barbosa、Nobuo Hosokawa、Hiroshi Naganawa、Tomio Takeuchi

  DOI：10.1016/s0040-4039(98)00426-2

  日期：1998.5

  The complete relative and absolute configurations of (+)-thiazinotrienomycin E, a potent new ansatrienin cancer cell growth inhibitory agent, have been determined via degradation and chemical correlation.

  已通过降解和化学相关性确定了（+）-噻嗪诺米诺霉素E（一种有效的新型ansatrienin癌细胞生长抑制剂）的完整相对和绝对构型。
• N-substituted mercaptopropanamide derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0318859A2

  公开（公告）日：1989-06-07

  Novel N-substituted mercaptopropanamide derivatives of the formula: wherein R₁ is mercapto or a group convertible into mercapto when cleaved within the biobody, W is hydrogen atom, an alkyl or an aralkyl, R₂ is an aryl which may optionally have substituent(s), a heterocyclic group which may optionally have substituent(s), or an alkyl which may optionally have substituent(s), X is a cycloalkylene, a cycloalkylidene, or a phenylene which may optionally have substituent(s) or may optionally be fused with other ring, and R₃ is carboxyl or a group convertible into carboxyl when cleaved within the biobody, or a pharmaceutically acceptable salt thereof, and a solid solution of said N-substituted mercaptopropanamide derivative with an amino acid, which have excellent enkephalinase inhibitory activity and are useful for the treatment of mild to moderate pain, and a pharmaceutical composition containing said compounds as an active ingredient, and processes for preparing these compounds.

  式中的新型 N-取代巯基丙酰胺衍生物： 其中 R₁ 是巯基或在生物体内裂解时可转化为巯基的基团，W 是氢原子、烷基或芳烷基，R₂ 是芳基（可选择具有取代基）、杂环基（可选择具有取代基）或烷基（可选择具有取代基），X 是环亚烷基、亚环烷基或亚苯基（可选择具有取代基）或可选择与其他环融合、和 R₃ 是羧基或在生物体内裂解时可转化为羧基的基团，或其药学上可接受的盐，以及所述 N-取代巯基丙酰胺衍生物与氨基酸的固溶体，它们具有优异的脑啡肽酶抑制活性，可用于治疗轻度至中度疼痛，以及含有所述化合物作为活性成分的药物组合物，以及制备这些化合物的工艺。
• WRINKLE-PREVENTIVE/AMELIORATING AGENT
  申请人：SHISEIDO COMPANY, LTD.

  公开号：EP1908454A1

  公开（公告）日：2008-04-09

  A wrinkle-preventing and -improving composition comprising one or more than one compound selected from the group consisting of α-amino acid derivatives represented by the following general formula (1) and salts thereof: wherein, R1 represents hydrogen atom, CH3 group or CH2OH group, R2 and R3 each independently represent hydrogen atom, alkyl group having 1 to 4 carbons, provided that R2 and R3 cannot be hydrogen atom at the same time, or R2 and R3 together with N atom to which they are bound may form a ring structure having a total carbon number of 4 to 6, in which case said ring structure may optionally contain an oxygen atom as a heteroatom, R4 represents hydrogen atom, alkyl group having 1 to 18 carbons, wherein when R1 and R4 are hydrogen atom, it cannot be that one of R2 and R3 is benzyloxycarbonyl group and the other is hydrogen atom.

  一种防皱和改善皱纹的组合物，包含一种或一种以上选自下式（1）所代表的 α-氨基酸衍生物及其盐类的化合物： 其中，R1 代表氢原子、CH3 基团或 CH2OH 基团，R2 和 R3 各自独立地代表氢原子、具有 1 至 4 个碳原子的烷基，但 R2 和 R3 不能同时为氢原子，或者 R2 和 R3 与它们所结合的 N 原子可形成一个总碳数为 4 至 6 的环结构、R4 代表氢原子或碳原子数为 1 至 18 的烷基，其中当 R1 和 R4 为氢原子时，R2 和 R3 不能一个为苄氧羰基，另一个为氢原子。
• KABATAKEH, SEHTSUKO;AONO, DZYUNITIRO;XINOXARA, JOSIKADZU;TANAKA, SADAO;KU+
  作者：KABATAKEH, SEHTSUKO、AONO, DZYUNITIRO、XINOXARA, JOSIKADZU、TANAKA, SADAO、KU+

  DOI：——

  日期：——
• TANAKA, SADAO;KUROMARU, SEHJSOKU;FUDZIMURA, YASUO;MATSUNAGA, ISAO;OBATA, +
  作者：TANAKA, SADAO、KUROMARU, SEHJSOKU、FUDZIMURA, YASUO、MATSUNAGA, ISAO、OBATA, +

  DOI：——

  日期：——